re: Getting contacted by work during vacation

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If so much money is at stake, why allow the process to be held up completely by one person?

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You can’t allow it, which is why it’s important that those things get handed off before someone leaves.

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I get that stuff happens, but at least after discovering the issue, this is one of the biggest reasons for cross training.

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Not everything can be fixed with cross-training. People can be cross-trained but unless you have actual redundancy built in (which nobody really does) you’ll still run into situations where one person can hold up the business.

Real-world examples I’ve dealt with personally:

- General counsel has inserted himself into a contract negotiation because of certain contentious terms. He goes on vacation in the middle of the negotiation. His subordinates can’t pick up the slack because there might be items they don’t have authority to approve (hence his involvement in the first place) and his manager can’t pick it up because he has no background on the deal. We don’t get two general counsels just so one can take vacation.

- Estimator is working on a bid that’s due next Tuesday but he’s on vacation next week. He says he’s going to get everything finished up Friday before he leaves, but he finishes too late for us to review. When we review Monday we find what appear to be issues or mistakes, but the estimator is already gone on vacation so we are unable to verify. We have other people who can do his job, but in order to properly vet the estimate they would basically have to start from the beginning (and there’s not time to do that).

- Engineer is working on a project for a customer and goes on vacation. We need a key piece of information to keep the project from getting held up, but we don’t know where exactly he saved that information because it’s on his desktop, or in his inbox.

These things can be avoided but it takes some amount of effort from the employee (as well as his/her manager) to make sure the business doesn’t get hung in their absence. Nobody - at least nobody I work with - wants to call anyone while they’re on vacation. But I’ve definitely seen occasions where it had to be done, and unfortunately most of the time it was probably avoidable with a little bit of planning.